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So before I showed my recreation of Bro Gamer's Champion Ash in MMD, courtesy of some edits of 's Kalos Ash. I figured eventually I needed to show off a roster of Pokémon to accompany him, and here's what I believe to be his biggest players, in order of acquisition:
Raichu: What's an Ash without a Chu? In this case, Bro had Ash eventually evolve him into a Raichu, turning him into an even bigger powerhouse than he was before. Also, this Ash still has a Pikachu to call on, who is the son of his trusty Raichu.
Pidgeot: After eventually upholding his promise to return, Pidgeot decided to return to Ash's roster, becoming one of his eight Mega Evolutions, as well as one of his most reliable. Also, I didn't realize how huge Mega Pidgeot was until I compared him to Ash. XD
Charizard: As we know, Charizard's training at the Charicific Valley was eventually completed during Ash's Unova venture. This meant that the flame lizard would earn a more permanent spot on Ash's roster. The reasoning I went for Y in this case is to contrast with Alain's Mega Charizard X.
Snorlax: Despite being such a huge glutton and Ash being unable to quell his humongous appetite, this guy has always been one of Ash's heaviest hitters throughout the Orange Islands as well as Hoenn and the Battle Frontier. Ice Punch in particular is mighty under his hands. He also holds an honor of being one of only five potential Pokémon to use a special Z-Move.
Heracross: Another out-and-out powerhouse, who can be an absolute beast if Mega Evolved. Heracross may have an affinity for Venusaur's sap, but he's got a good heart and always tries his best in battle.
Noctowl: This bird may not be the best of Ash's Pokémon, but she was his one Shiny, and he always treats her with the respect she deserves. After all, don't all Trainers remember their first Shiny fondly?
Donphan: This one I'm most disappointed in model-wise, but that's because the model isn't even rigged. Oh well. Donphan helped Ash quite a bit in the Battle Frontier, and, being his first hatched Pokémon, also treats him with plenty of care.
Sceptile: Ash's fourth faithful Mega Evolution, Sceptile may have had a lapse of confidence after failing to win over a Meganium, but after he regained his sense of worth he proved time and again to be a powerful fighter. He may fear Ice the most, but Charizard and Infernape are willing to torch any Ice-type that threatens the gecko.
Infernape: This monkey may have had a terrible first trainer, but he was able to quickly get his vengeance against Paul during the Sinnoh League, proving himself to everyone by taking on most of his nemesis' team on his own. He may not be able to go Mega, but with Blaze providing a powerful boost he doesn't need a Mega Stone to trounce a team.
Krookodile: Even though Champion Ash managed to evolve all his Pokémon in Unova, Krookodile still proved to be one of the strongest of his team. The Dark croc not only has those shades to tell everyone he's not to be messed with, he can back those claims up with extreme ease by shaking the earth and/or biting the enemy into submission.
Greninja: Ah, who could forget the frog? Greninja could easily be Ash's strongest Pokémon, and with good reason: Battle Bond can be absolutely devastating when played properly. He can take on pretty much everyone and, at worst, come out with a Double KO.
Goodra: While Greninja may be the strongest, Goodra is undoubtedly the bulkiest. He can soak up plenty of damage and unleash a mighty Bide that will almost certainly take down the enemy. Even against Sawyer's Slurpuff that ended in a draw. That's some power.
Noivern (Honorable Mention): He didn't have many battles, but I think Noivern still deserves a spot on the roster, at least concerning the "Still Owns" list. Barring Mega Sceptile, Noivern is only one of two Dragon-types Ash still owns (the other being Gible/Garchomp), so he doesn't really many options for that type anyway.

Ash, Mega Charizard Y, Ash-Greninja, and Goodra by
Raichu, Mega Pidgeot, Snorlax, Noctowl by
Heracross, Infernape, and Krookodile by
Mega Sceptile by . I didn't even realize there was a Mega Sceptile model until not too long ago. Admittedly it's the Pokkén one instead of OR/AS or S/M, but I'll take what I can get.
Donphan provided by , but it sadly remains unrigged.
Daisy Cruiser by
Effect: SSAO

EDIT 8/13: Switched regular Sceptile with the Mega version when I found out there was one rigged and ready to go. Here's hoping Mega Heracross gets the same treatment!
Also, I may add in Noivern eventually as, while he may not be among the best, I tend to see Ash's main six for those that he owns as Pika/Raichu, Snorlax (Z-Move), Sceptile (Mega), Infernape, Krookodile, and Noivern. Aside from possibly Snorlax all the Pokémon are from different regions, which was my main goal for Ash's all-star roster.

Description
So before I showed my recreation of Bro Gamer's Champion Ash in MMD, courtesy of some edits of 's Kalos Ash. I figured eventually I needed to show off a roster of Pokémon to accompany him, and here's what I believe to be his biggest players, in order of acquisition:
Raichu: What's an Ash without a Chu? In this case, Bro had Ash eventually evolve him into a Raichu, turning him into an even bigger powerhouse than he was before. Also, this Ash still has a Pikachu to call on, who is the son of his trusty Raichu.
Pidgeot: After eventually upholding his promise to return, Pidgeot decided to return to Ash's roster, becoming one of his eight Mega Evolutions, as well as one of his most reliable. Also, I didn't realize how huge Mega Pidgeot was until I compared him to Ash. XD
Charizard: As we know, Charizard's training at the Charicific Valley was eventually completed during Ash's Unova venture. This meant that the flame lizard would earn a more permanent spot on Ash's roster. The reasoning I went for Y in this case is to contrast with Alain's Mega Charizard X.
Snorlax: Despite being such a huge glutton and Ash being unable to quell his humongous appetite, this guy has always been one of Ash's heaviest hitters throughout the Orange Islands as well as Hoenn and the Battle Frontier. Ice Punch in particular is mighty under his hands. He also holds an honor of being one of only five potential Pokémon to use a special Z-Move.
Heracross: Another out-and-out powerhouse, who can be an absolute beast if Mega Evolved. Heracross may have an affinity for Venusaur's sap, but he's got a good heart and always tries his best in battle.
Noctowl: This bird may not be the best of Ash's Pokémon, but she was his one Shiny, and he always treats her with the respect she deserves. After all, don't all Trainers remember their first Shiny fondly?
Donphan: This one I'm most disappointed in model-wise, but that's because the model isn't even rigged. Oh well. Donphan helped Ash quite a bit in the Battle Frontier, and, being his first hatched Pokémon, also treats him with plenty of care.
Sceptile: Ash's fourth faithful Mega Evolution, Sceptile may have had a lapse of confidence after failing to win over a Meganium, but after he regained his sense of worth he proved time and again to be a powerful fighter. He may fear Ice the most, but Charizard and Infernape are willing to torch any Ice-type that threatens the gecko.
Infernape: This monkey may have had a terrible first trainer, but he was able to quickly get his vengeance against Paul during the Sinnoh League, proving himself to everyone by taking on most of his nemesis' team on his own. He may not be able to go Mega, but with Blaze providing a powerful boost he doesn't need a Mega Stone to trounce a team.
Krookodile: Even though Champion Ash managed to evolve all his Pokémon in Unova, Krookodile still proved to be one of the strongest of his team. The Dark croc not only has those shades to tell everyone he's not to be messed with, he can back those claims up with extreme ease by shaking the earth and/or biting the enemy into submission.
Greninja: Ah, who could forget the frog? Greninja could easily be Ash's strongest Pokémon, and with good reason: Battle Bond can be absolutely devastating when played properly. He can take on pretty much everyone and, at worst, come out with a Double KO.
Goodra: While Greninja may be the strongest, Goodra is undoubtedly the bulkiest. He can soak up plenty of damage and unleash a mighty Bide that will almost certainly take down the enemy. Even against Sawyer's Slurpuff that ended in a draw. That's some power.
Noivern (Honorable Mention): He didn't have many battles, but I think Noivern still deserves a spot on the roster, at least concerning the "Still Owns" list. Barring Mega Sceptile, Noivern is only one of two Dragon-types Ash still owns (the other being Gible/Garchomp), so he doesn't really many options for that type anyway.

Ash, Mega Charizard Y, Ash-Greninja, and Goodra by
Raichu, Mega Pidgeot, Snorlax, Noctowl by
Heracross, Infernape, and Krookodile by
Mega Sceptile by . I didn't even realize there was a Mega Sceptile model until not too long ago. Admittedly it's the Pokkén one instead of OR/AS or S/M, but I'll take what I can get.
Donphan provided by , but it sadly remains unrigged.
Daisy Cruiser by
Effect: SSAO

EDIT 8/13: Switched regular Sceptile with the Mega version when I found out there was one rigged and ready to go. Here's hoping Mega Heracross gets the same treatment!
Also, I may add in Noivern eventually as, while he may not be among the best, I tend to see Ash's main six for those that he owns as Pika/Raichu, Snorlax (Z-Move), Sceptile (Mega), Infernape, Krookodile, and Noivern. Aside from possibly Snorlax all the Pokémon are from different regions, which was my main goal for Ash's all-star roster.